Boron tribromide → HCID 20531732, compound

Participants

Reaction Steps

The N-allyl trimethoxy base (VII) (2.4 g, 0.0064 m) was dissolved in 50 ml of methylene chloride and mixed with a solution of 6.0 ml (0.64 m) of boron tribromide in 40 ml of methylene chloride at -15°. After stirring for 2 hours at room temperature, the mixture was cooled and quenched with methanol several times, the last time with 4 drops of 48% hydrogen bromide added. Final evaporation gave a foam which was dissolved in ethyl acetate-methanol. The mixture was heated at reflux briefly then cooled to give 1.5 g (52%) of 2-allyl-8-chloro-6,7-dihydroxy-4-(p-hydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide, m.p. 252°-254° (d.).

Provenance & Evidence